Phoebe's half-brother visits, but they have trouble bonding. Joey attempts to build an entertainment center. Ross is challenged to name the five celebrities he'd like to sleep with most.

Ross and Rachel compete to spend time with their other friends. When a lonely Ross is excluded from Rachel's ski trip with her pals, he visits Carol. On the way to the cabin, they run out of gas. Meanwhile, Chandler starts smoking again.

When Rachel finds out that Ross is bringing a date to the premiere of Joey's big play, she finds one of her own. Ross alone concludes that her date is insane. Poor Phoebe is on hold for days with a company she needs to talk to before her phone warranty expires. Meanwhile, Joey's play gets terrible reviews, but his co-star provides some comfort.

Ross's new girlfriend seems nearly perfect until he visits her house and discovers that her apartment is incredibly dirty. Chandler helps Joey pick out a thoughtful present for Kathy's birthday. Rachel attempts to finish a crossword puzzle by herself. And Phoebe helps Monica cater a funeral.

Ross must decide whether to continue dating a girl he must travel two-and-a-half hours to see. Chandler sets Rachel up with a co-worker who misunderstands her intentions. Monica is being treated poorly by her new co-workers so she hires Joey just so she can fire him and show who's the boss. And Phoebe tries to write the perfect holiday song.

Ross proposes to Emily. Monica and Rachel try to win their apartment back from Chandler and Joey.

Monica and Chandler plan an Atlantic City getaway in order to have an intimate weekend away from their friends. Meanwhile, Ross prepares himself to tell Rachel that he can't see her anymore.

On the last night before Chandler and Monica move in together, Monica and Rachel argue, while Chandler tries to give Joey money to help him pay the upcoming bills.

Ross meets Elizabeth's father for the first time and unfortunately he takes an instant disliking to Ross. However Paul does hit it off with Rachel and she tries to talk Ross up but does so with mixed results. Joey almost gets fired from "Mac and C.H.E.E.S.E." after offending the operator of the robot. Meanwhile, Phoebe writes a book based on Monica and Chandler.

Chandler plans to propose to Monica at dinner, but his plans go awry when Richard shows up at the same restaurant. Meanwhile, Phoebe and Joey join Rachel at a charity auction only to discover that Joey isn't aware what a silent auction is. And Ross and Elizabeth's relationship comes to a crossroad.

Chandler continues to pretend to hate the idea of marriage, unaware that Richard wants Monica back. Meanwhile, Rachel and Phoebe discuss their 'back-up' plans, if they are not married by the time they're 40.

Rachel and Phoebe befriend a girl Joey's dating and they try to convince him to get more serious with her, however he's reluctant to do so. At least at first. Meanwhile, Ross discovers that his doctoral dissertation is hosted at university's library and is very excited about the fact. Unfortunately, he soon finds out that students aren't exactly reading it, but rather engaging in other 'physical activities' in the paleontology section. Also, Monica runs into Janice and before she knows it, Janice has invited herself to Monica's wedding. Needless to say that neither she nor Chandler aren't exactly ecstatic about it and they both try to find a way to tactfully uninvite her.

At Central Perk Rachel runs into her friend from college, Melissa, and it turns out they share something more than just a friendship. Meanwhile, Monica plans the seating arrangement for the wedding and is taken by surprise when Joey mentions that his parents are coming to the wedding too. Also, Chandler and Ross argue who gets to wear a celebrity tux for the event.

Monica and Chandler return from their honeymoon with stories of a couple that they met on the flight back, but soon discover that the couple gave them a wrong number. Meanwhile, Ross and Rachel tell everyone about the night they were together, however, their stories differ as to who made the first move. While Ross emphatically defends his side of the story, he accidentally reveals that he has the encounter on videotape. Unsurprisingly, everyone wants to see it.

Ross and Rachel go to the hospital to have their baby, but it's a long labor. They get stuck in a semi-private room, and many other couples come and go before Rachel is ready to deliver - the last couple being Janice and her new husband. Meanwhile, Chandler and Monica decide to start trying to have a baby, but can't find an empty hospital room where they wouldn't be disturbed. Also, Phoebe meets a handsome stranger and "recruits" Dr. Drake Ramoray to gather some personal information about him.

After Rachel gives birth to her little baby girl, she must confront relationship issues around her. So does Ross, who gets an engagement ring from his mother, while she urges him to propose to Rachel. The things, however, take an interesting turn.

The friends are looking forward to getting together and celebrating Phoebe's birthday. However, on the day of the party, Ross struggles to convince Rachel to leave Emma with Mrs. Geller babysitting, and Monica and Chandler get into an argument, after Monica discovers that he's been smoking. All of this causes them to be incredibly late, leaving Phoebe and Joey alone at a restaurant with a table for six.

Chandler gives David advice that culminates in David deciding to propose to Phoebe. However, Phoebe is still in love with Mike. Monica meddles and calls Mike, who shows up in Barbados and interrupts David's marriage proposal with one of his own. Phoebe chooses Mike, although she doesn't accept his proposal. Meanwhile, sparks fly between Ross and Charlie when they spend some time together rewriting his speech.

Charlie and Joey break up, and Rachel finally tells Joey about her crush on him. He decides nothing can happen because Ross is a good friend, but after he sees Ross and Charlie kissing, he heads back up to Rachel's room where the two kiss and shut the door. Meanwhile, Monica and Mike compete at a game of ping pong.

Monica and Chandler travel to Ohio to meet a young pregnant woman, Erica Simmons, who is considering allowing them to adopt her child. Due to a mix-up at the adoption agency, Erica thinks Monica is a reverend and Chandler is a doctor. Joey dates Phoebe's friend but annoys her with his territorial eating habits. Rachel picks out an outfit for Ross to wear on a date but he ends up in a unique new wardrobe.